Textile lubricating compositions



United States Patent 2,824,832 Patented Feb. 25, 1958 fifice TEXTILE LUBRICATENG COIVIPDSITIONS Henry F. Leupold, Nutley, and Qharles H. Lighthipe, Bloomfield, N. J., assignors to Nopco Chemical OEB= puny, Harrison, N. L, a corporation of New Jersey No Drawing. Application October 21, 1953 Serial No. 387,531

14 Claims. (Cl. 252-33) This invention relates, in general, to new and improved textile lubricating compositions. More particularly, the invention relates to the treatment of wool and worsted materials with our novel lubricating compositions.

The conventional commercial processes by which woolen and worsted cloth are manufactured, as well as those by which other cloths are manufactured, are quite complex. In general, these processes involve an integrated series of steps which accomplish the desired result in the most efiicient manner possible. The manufacture of cloth from wool, worsted and like material has its inception with the shearing of sheep and other wool bearing animals. However, the actual conversion of the wool into cloth begins when the fleece is washed and dried and when the fibers thus obtained are sorted into the various groups according to their color and their quality. Thereafter, the selected fibers are treated, usually by spraying or immersion, with a lubricating composition. After the oiling of the wool is completed, the fibers are subjected, in sequence, to the various steps involved in the combing or carding process and thereafter to the spinning process. The primary purpose of the carding step is to arrange the fibers in a parallel formation. However, an incidental, but yet highly important function of this step, is to remove foreign matter from the fibers. Prior to spinning, the fibers are drawn into strands. In the spinning operation the strands are twisted into yarn. By subsequently subjecting the twisted strands to a steam treatment a twist is set into the yarn. The spun yarn is then woven on looms into cloth. Weaving of the yarn, however, is not the final step in the process since the woolen fabric produced in the weaving step is comparatively loose and thin in structure. To correct this, the fabric is subjected to a process commonly referred to as fulling. In this step the fabric is thickened and shrunk by agitating it in an aqueous soap solution. Following the fulling step, the fabric is scoured to remove the lubricating composition which was applied to the fibers prior to the carding step. Thereafter, the material is dyed, dried and ordinarily steam finished.

Quite obviously, the operations involved in the manufacture of woolen and worsted cloth from the fibers are such that the selection of a proper lubricating composition is of primary importance. This lubricant must satisfactorily lubricate or oil the wool or worsted fibers throughout all of the various steps involved in the manufacture of fabrics therefrom. However, the suitability of a particular composition for use as a textile lubricating oil is not determined merely by the ability of the composition to satisfactorily lubricate the fibers. Very many other important factors must be taken into consideration. Thus, in addition to being a satisfactory lubricant, the composition chosen for use must be of such a nature that the accumulation of charges of static electricity developed during the steps of the process, particularly during the car-ding step, are kept at an absolute minimum. Serious technical difficulties will ensue in the mill if static is not controlled. Moreover, thecomposition employed as the W001 lubricant must neither discolor, nor tend to discolor, the yarn under the conditions encountered in the various steps involved in the manufacture of the fabrics. Furthermore, the wool lubricating composition employed must be, readily emulsifiable in water and it must be such that it can be readily and completely removed from the fabrics during the scouring step of the process.

Many wool lubricating oils have heretofore been disclosed in the art. However, for various reasons, a large majority of these have been found to be unsatisfactory. Thus, for example, many of the prior art compositions have been far too expensive to make their use in a textile mill economical or practical. Also, many of the prior art products either failed to lubricate the fibers satisfactorily or were ineflective in reducing the static electricity produced during the carding step. Furthermore, the use'of several of the prior art products would have necessitated certain changes in the well established procedures employed in the industry.

It is the object of this invention to provide novel, completely satisfactory wool lubricating compositions.

It is another object of this invention to provide relatively inexpensive wool lubricating comnositions which neither discolor, nor tend to discolor, the yarn treated therewith and which materially reduce the charges of static electricity produced during the various steps of the process.

A further object of this invention is to provide an economical wool lubricating composition which can be readily removed from the fabric produced by conventional scouring processes.

A more particular object of the invention is to provide readily emulsifiable wool lubricating compositions, the highly concentrated aqueous emulsions of which are relae tively low in viscosity and are extremely stable.

Other objects of this invention will be obvious and will in part appear hereinafter.

We have found that compositions which comprise a blend of (l) a product produced by condensing ethylene oxide and an alkylated phenol, (2) a blown oil, (3) a mineral oil, and (4) a fatty acid or a mixture of a fatty acid and a fatty acid ester are highly superior wool or worsted lubricating oils.

The condensation products which are present in our novel products are those which are produced by the condensation of ethylene oxide and an alkylated phenol. In its broadest aspect, the present invention embodies the use of condensation products produced by condensing at least equimolar quantities of ethylene oxide with an alkylated phenol. However, if desired, a condensation product can be employed which has been produced using as many as 12 moles of ethylene oxide or more for each mole of alkylated phenol. The condensation product preferably employed in formulating our novel products are those which have been prepared using from about 8 to about 10 moles of ethylene oxide for each mole of alkylated phenol. The phenolic compounds employed in the preparation of these condensates are alkyl substituted phenols, the alkyl groups of which have carbon chain lengths of from about 4 to about 12 carbon atoms. The preferred condensates used in the invention are prepared, however, from alkyl phenols having a carbon chain length of 8 or 9 carbon atoms. Thus, for example, condensates prepared by reacting ethylene oxide with phenols such as, octyl phenol, nonyl phenol, decyl phenol, dodecyl phenol, etc., can be employed. The preparation of the condensate is not, of course, part of the present invention and, hence, the invention should not be construed as restricted to the use of condensation products produced by any particular method. Rather, it should be understood that our novel wool lubricating compositions can be produced using ethylene oxide-alkylated phenol condensates prepared by any suitable method known in the art. In the production of the wool lubricating compositions of the present inven tion, the ethylene oxide-alkylated phenol condensation products comprisebroadly, from about 8% to about 25% by weightof the product. However, the preferred compositionsoflthe invention contain from about 11%..to Tabout il%1by weight of the ethylene oxide-alkylated phenol condensate; j i

:Y'The new and 'i proved productsfof our invention also contain a blown oil; The expression blown-oil is-used herein to c'onnote any non-drying or semi-drying animal or; vegetable oil, fat or wax which has been partially or "completelyoxidized and/ or'polymerized. These blown :oils maybe prepared by any known and suitable process. Examples of some of theo'ils which can be used in the productionjo'f our products are blown castor oil, blown corn oil, "blown cottonseed oil, blown neats-foot oil, blown'peanut oil, blown rapeseed oil, blown-rice bran Qoil, blown teaseed o'il, blown lard oil. Moreover, mixtures. of anytwoeor more of these oils with each other or withotherblown oils of the types disclosed canbe employed. The blown oil constituent described herein' comprises broadly from about to about 35% by 'weight of the final product. Preferably, however, the novel products of-the invention contain from about 18% to about 26% by weight of a blown oil or of mixtures of blown oils.

Our novel compositions also contain as an essential ingredient' thereof a mineral oil. In general, any mineral oil can be employed whose properties and characteristics are such that it is generally suited for use in textile treating "compositions; Thus, for example, the use of mineral oils having relativelylow viscosities and which are reasonably light in color is generally unobjectionable in compositions designed for usein treating textiles. Mineral oils having these characteristics are the ones contemplated by the present disclosure. Especially well suited for use in preparing ourcompositions are white mineral oils and pale paraffin oilswhich have a viscosity which varies within the range of from about 50 Saybolt seconds at 100 F. to about 300.Saybolt secondsrat 100 F. In preparing the preferred compositions of the invention, however, a

'white mineral oil having a viscosity of about 200 Saybolt seconds at 100 F. is employed. 'The mineral oil con stituent of our'products comprise from about 45% 'to about 65 by Weight'of our products. Howeven the wool lubricating compositions of our invention preferably contain from about 50% to about 60% by weight of mineral ,oil. i

i The final constituent ingredient of our novel wool or worsted lubricating oils is a fatty-type material. This constituent ofour products can be (1) a fatty acid or a' mixture of fatty acids, or, (2) a mixture. of one or more fatty acids with one or more esters of fatty acids.

; material used in the formulation of ournovel products,

that is either the fatty'acidor the fatty acid-fatty acidester mixture, is .one' which is liquid or substantially liquid attempera'tures at or around 'room temperature. The fatty materialused in preparing the preferred compositions of this invention is oleic acid. However, other liquid fatty acids, such as, caprylic acid, capric acid, etc.

and non-liquid fattyacids such as palmitic acid, stearic' acid andthe like, as well as mixtures thereof, can be used; When linoleic acid and linolenic acid are used in formulating our novel compositions, they are, because of h kk 'va staea ,s ntencedwmbiaafiaawhh.

' The precise sequence in which the various constituent our novel wool or WOITSICCl lubricating compositions. i

Preferably, however, the novel. compositions or the invention contain. from about 8% to about 12% by weight of a fatty material of this type. When the fatty component of our novelcomposition is a fatty acid-fatty acid ester mixture, the estercomponent of the mixture can comprise up to about 80% by weight 'of the total weight 7 of the fatty mixture.

ingredients are admixed in producing the present products is not-atall critical to the operability of the invention. The actual blending, however, is'ordinarily accomplished at room temperature by completely and thoroughly stir-.

ring together. the components which make up the blend.

Ifdesired, theblending of the mass into a homogeneous productcan be carried out at temperatures higher than room temperature although generally the use of such high temperatures is entirely unnecessary.

In general, the compositions of this invention can be used in treating all animal, vegetable and synthetic fibrous material. These compositions have been designed, however, particularly for the treatment of wool and worsted. .Thecompositions can be applied to thevfibers by anyof the conventional means presently employed in the art, at any point in the manufacturing process prior to the. spinning step. However since the present products function so'eflfectively as anti-static agents, full benefit accrues from the use of these compositions when the fibers are treated with said compositions prior to the carding step. When the present products are employed it is never necessary to treat the fibers with a separate anti-staticv agent. Moreover, after the fibers have been carded, spun,

woven and after the fabric has been fulled, the lubricatnig compositions of the present invention are readily and completely removed by any of the conventional'scouring processes known and used today. p g g The physical characteristicsand the properties. of the compositions of the present invention are such thatthey are highly suited for use in thetreatment of textiles.

.Thus allof the products of the invention are at elevated temperatures clear, fluid materials. They are readily emulsified in water without the aid'of conventional emulsifying agents. None;of the compositions discolor, or tend to discolor the yarn treated therewith. Moreover,

these products are heat stable since they retain their phy i sical and chemicalcharacteristics after being heated at a temperature of about C. for a period in'excess of aboutone Week. It has'been found that emulsions of our compositions, including those which have a concen tration of up to about 50% by weight, are stable for periods of times in'excessiofabout 24 hours. Because of the outstanding emulsion stability of the presentproducts they can be applied'to' the textile fiber very effectively by any of the conventional processes.- Moreover," since,

when emulsified in water, even at concjentrationsranging from 10% to about 50% by weight,.our products form free'fiowing liquids, the fibers can be treated; in conven-" tional fashion, with substantially smaller volumes ofthe more highly concentrated emulsions of .our productslwith complete'satisfaction. Moreover, since even the more highly concentrated emulsions of: the .productsof the present invention are liquids, these.concehtratdiemul sions can' be' applied to, the fibers ;by, spraying. Thisis: not possible-when many of the prior art products are employed to lubricate the fibers because of the extremely viscous nature of the vhighly concentrated emulsions of said productay Thus, when .the prior :art products are applied to textile fiber by spraying, the emulsions used are of necessity usually relatively quite dilute. Furthermore, not only are the lubricant compositions of the present invention easily applied to the fibers but also they are very readily removed from the fabric when they have served their purpose. When employing the present compositions it is never necessary to devise new methods for removing the lubricant since the properties of the compositions of our invention are such that they can be removed from the fabrics by conventional scouring methods.

It is not known precisely why our novel products have such outstanding charcteristics since several of the ingredients which comprise our products have been used heretofore in combination with each other and other materials without exhibiting such a combination of outstanding properties. It is known, however, that our compositions, due to their stability, their emulsifiability, their anti-static character and their lubricating properties and particularly because of the stability and low viscosity of aqueous emulsions thereof, are extremely outstanding lubricating compositions.

For a fuller understanding of the nature and objects of our invention, reference should be had to the following examples which are given merely as further illustrations of the invention and are not to be construed in a limiting sense. All parts are given by weight.

Example I In this example, a mixture of 55 .0 parts of mineral oil having a viscosity of 200 Saybolt seconds at 100 F. and 22.0 parts of blown rice oil was originally prepared. These materials were blended together at room temperature with constant stirring. Thereafter, 13.0 parts of a condensate prepared by reacting about 8.5 moles of ethylene oxide with 1.0 mole of octyl phenol were added to the mixture of blown and mineral oils. This addition was carried out with continual stirring and at room temperature. To this mixture, 10.0 parts of oleic acid were added at room temperature. The solution which was formed was stirred until homogeneous.

This product was a clear, light amber colored liquid at room temperature. Emulsions of this product (concentrations thereof being between to 50% by weight of the product) were free flowing liquids. 10%, 33% and 50% aqueous emulsions of the product were exceedingly stable. When observed at a period of time substantially in excess of 24 hours, these emulsions showed no tendency whatsoever to break.

Evaluation of this product as a wool or worsted oil was carried out using conditions actually encountered in a textile mill. Thus, an aqueous emulsion consisting of about 80% by weight of water and 20% by weight of the wool oil of this example was initially prepared. It was first observed that this emulsion was a free flowing liquid capable of being applied either by spraying or by dripping onto the fibers. This emulsion was then used to oil worsted fibers. It was applied to the fibers immediately preceding the carding step. The static controlling properties of this product were carefully observed and it was found that the wool oil of this example was satisfactory in every respect and was superior to many of the anti-static wool oils commercially used today. Furthermore, it was noted that greatly increased efi'lciency resulted during the spinning step of the process due to the use of product. It was found that when t e worsted fibers were treated with the emulsion of the present product from about 10% to about less breaks in the fibers occurred than will normally occur when worsted fibers, treated with conventional lubricating compositions, are spun. It was further round that the performance of this product during weaving was very satisfactory, the results obtained being superior to the results obtained with many conventional wool oils. Moreover, it was observed that the product of this example was readily and completely removed from the woven fabric by conventional scouring processes.

Example 11 In this example 17.1 parts of blown peanut oil were added to 57.1 parts of a mineral oil having a viscosity of 200 Saybolt seconds at F. These materials were blended together by stirring. Thereafter, 13.3 parts of a condensate prepared by reacting about 8.5 moles of ethylene oxide and 1.0 mole of octyl phenol were added to the mixture of blown and mineral oils. This addition was carried out at room temperature with continual stirring. To this mixture, 12.5 parts of oleic acid were added at room temperature. The solution which was formed was stirred until homogeneous.

This product was a clear, light amber colored liquid at room temperature. Emulsions of this product were free flowing liquids and were exceedingly stable. The product was found to be an excellent wool lubricating composition. It possessed excellent anti-static properties and was completely removable from wool by conventional scouring processes.

Example III In this example 20.8 parts of blown rice oil were added to 60.5 parts of a pale paraifin oil having a viscosity of 100 Saybolt seconds at 100 F. This mixture was thoroughly stirred. Thereafter, 15.6 parts of a condensate of about 8.5 moles of ethylene oxide and 1.0 mole of octyl phenolwere added to the blown oil-parafiin oil mixture with stirring. To this mixture, 3.1 parts of oleic acid were added and the solution thus obtained was stirred until homogeneous.

This product was a clear, light amber colored liquid at room temperature. Emulsions of this product were free flowing liquids and were exceedingly stable. This product exhibited outstanding wool lubricating and static controlling properties. It was readily removable from Wool by conventional scouring processes.

Example IV In this example a mixture of 25.0 parts of blown rice oil and 55.0 parts of a mineral oil having a viscosity of 200 Saybolt seconds at 100 F. was initially prepared. The mixture was stirred thoroughly. To this mixture 13.7 parts of a condensate prepared by reacting about 8.5 moles of ethylene oxide with 1.0 mole of octyl phenol were added. This blend was thoroughly stirred. Thereafter 6.3 parts of stearic acid were added to the mixture following which the blend was stirred thoroughly until homogeneous.

This product was a clear, slightly viscous, light amber colored liquid at room temperature. Emulsions of this product were free-flowing liquids and extremely stable. This product possessed excellent wool lubricating and static controlling properties. Furthermore, it was readily removable from wool by conventional scouring processes.

On standing for an extended period of time, this product became hazy. Its clarity, however, was readily restored by gently warming it.

Example V In this example, a mixture or" 20.4 parts of blown rice oil and 51.0 parts of a mineral oil having a viscosity of 200 Saybolt seconds at 100 F. was initially prepared. This mixture was stirred thoroughly. Thereafter, 13.3 parts of a condensate produced by reacting 8.5 moles of ethylene oxide with 1.0 mols of octyl phenol were an free flowing liqnids and exceedingly-stable; The

product was an excellent wool oil andanti-static agent.

i It was readily removable from wool by conventional wm rmmm- H E xample VI 7 K In this example a mixture of 20.0"parts of blown rice oil and 55.0 parts of mineral oil having a viscosity of about 200 Saybolt seconds at 100 F. was produced.

This mixture was'thoroughly stirred. To this blend, 15.0 parts of a condensate prepared by reacting about 10.0

moles of ethylene oxide with 1.0 mole of nonyl phenol were added with stirring. Thereafter, 10.0parts of oleic acid .were added-to the mixture. The solution obtained.

of a blown oil selected from the group consisting of blown semi-drying oils and blown non-drying oils (2) from about.45% to about 65% by weight of a mineral oil having a viscosityof from about 50 to about- 300 Saybolt seconds at 100 F. (3) from about 8% to about 25% by Weight of a product produced by condensing at least equimolar proportions of an alkyl phenol and ethylene oxide, the alkyl groups in said alkyl phenol having from about 4 to about 12 carbon atoms in their carbon chain and (4) from about 3% to about 17% by weight of a fatty material selected from the group consisting of a fatty acid having a carbon chain length of from about 8 to about 22 carbon atoms, mixturesof said fatty 'acids,'and

mixtures of said fatty acids with esters prepared by react-i ing a fatty acid having a ,carbon'chain length of from about 8 to about 22 carbon atoms'and-mixtures thereof with monohydric aliphatic alcohols having a carbon chain of from 1 to about 5 carbon atoms. a g 2. The composition of claim 1 in which the ethylene oxide-alkyl phenol condensate is a productproduced by condensing one mole of an alkyl phenol with up to about 1'2 moles of ethylene oxide.

'3. A textile lubricating composition comprising from a about 18% to about'26% by weight of a blown oil selected from the group consisting'of blown semi-drying oils'and blown non-drying oils, from about to about 6 0% by weight of a mineral oil having a viscosity of from about 50 to about 300 Saybolt seconds at 100 F.,

from about 11% to about 15% by weight of a product produced by condensing one mole of an alkyl phenol with up to about 12 moles of ethylene oxide, the alkyl groups in said alkyl phenol having from about 4 to about 12 carbon atoms in their carbon chain and from about 8% to about 12% by weight of a fatty material. selected from the group consisting of a fatty acid having a carbon chain length of from about 8 to 22'carbon atoms, mixtures of said fatty acids, and mixtures of said fatty acids with esters prepared by reacting a fatty acid having a carbon chain length of from about 8 to about 22 carbonatoms. and mixtures thereof with monohydric aliphatic alcohols having a carbon chain length 'of from 1 to about 5 car bon atoms. 7

4. The composition of claim 3 wherein'theblown oil is a blow semi-drying oil. 7

5. The composition of claim 3 wherein the blown oil is a'bloWn non-drying oil. V

' 6. The-composition of claim 3 wherein the fatty material is a fatty acid .having a carbon chain length of from about 8 to 22 carbon atoms, said fatty acid beingtliiiuid at room temperature.

The composition of claim 3 whereiii the fatty material is a mixtureof fatty acids each of which has a'chain length of from about 8 to 22 carbonatoms, said fatty acid mixture being liquidat room temperature.

8. The composition of claim'3 wherein the fatty mate rial is a mixture of fatty acids and fatty acid; esters said fatty acids having a carbon chain length of from about '8 to 22 carbon atoms and said fatty acid esters having been prepared'by reacting a fatty acid having a carbon. chain length of from about'8 to 22 carbon atoms witha monohydric aliphatic alcohol havinga carbon chain length of from 1 to 5 carbon atoms, the ester in said mixture comprising up to about by weight of the mixture, said fatty acid-fatty ester mixture being liquid at room tem-.

perature.

9. The composition of claim 3 wherein the mineral oil is a white mineral oil having a viscosity of about 200 Saybolt seconds at 100 F. I

10. A textile lubricating composition comprising from about 18% to about 26% by weight'of blown rice oil, from about 50% to about 60% by weight of a mineral oil having a viscosity of about 200 Saybolt seconds at 100? 17",, from about 11% to about 15 by weight of a condensate prepared by reacting about moles of V ethylene oxide with 1.0 mole of octyl phenol and. from about 8% to about 12% by weight of oleic acid.

11. A.textile lubricating composition comprising from about 18% to about 26% by weight of blown peanut oil, from about 50% to about 60% by weight of a mineral oil having a viscosity of about 200 Saybolt seconds'at "F., from about 11% to about 15% by weight of a1 condensate prepared by reacting from about 8.5 moles of ethylene oxide with 1.0 mole of octylphenol and from about 8% to about 12% by weight of oleic acid.

12. A textile lubricating composition comprising from about.18% to about 26% by. weight of blown rice oil,

from about 50.% to about 60% by .weight' of a mineral 7 oil having a viscosity of. about 200 Saybolt seconds at 100. F., from about 11% to about 15% by weight 'of a condensate "prepared by reacting about 8.5 moles, of ethylene oxide with 1.0 mole of octyl phenol and from about 8% to about 12% by weight of stearic acid.

13 A textile lubricating composition comprising from 7 about 18% to about- 26% by weight-of blown rice oil,

from about 50% to about 60% by weight of a mineral oil having a viscosity of about 200 Saybolt seconds at 100 F., from about'1l% to about 15% by weight of a condensate prepared by reacting about 8.5 moles of ethylene oxide with 1.0 mole of octyl phenol and from about 8% to about 12% by Weight of a mixture consisting of about 80% by weight of oleic acid' methyl ester and 20% by weight of 'oleic acid.

14. A textile lubricatingcomposition comprising from V about 18 to about 26%. by weight of blown rice oil, from about 50% to about 60% by weight 'of a mineral oil having a viscosity of about 200 Saybolt seconds at 100 7 F., from about 11% to'about 15% by weight of a condensate prepared by reacting about 10.0 moles of ethylene oxide with 1.0'moleof nonyl phenol and from about 8% to about 12% by weightof oleic acid.

References Cited in the file of this patent UNITED STATES PATENTS 1,970,578 Schoeller Aug. 21, 1934 2,176,402 Koch Oct. 17, 1939 2,213,477 Steindorff et al Sept. 3, 1940 2,385,423 Seymour et a1 Sept. 25, 1945' OTHER REFERENCES Goldsmith: Non-Ionic Surface Active Agents, article in Chemical Industries, March 1943, pages 326-328. 

1. A TEXTILE LUBRICATING COMPOSITION WHICH COMPRISES A BLEND OF (1) FROM ABOUT 10% TO ABOUT 35, BY WEIGHT OF A BLOWN OIL SELECTED FROM THE GROUP CONSISTING OF BLOWN SEMI-DRYING OILS AND BLOWN NON-DRYING OILS (2) FROM ABOUT 45% TO ABOUT 65% BY WEIGHT OF A MINERAL OIL HAVING A VISCOSITY OF FROM ABOUT 50 TO ABOUT 300 SAYBOLT SECONDS AT 100* F (3) FROM ABOUT 8% TO ABOUT 25% BY WEIGHT OF A PRODUCT PRODUCED BY CONDENSING AT LEAST EQUIMOLAR PROPORTIONS OF AN ALKYL PHENOL AND ETHYLENE OXIDE, THE ALKYL GROUPS IN SAID ALKYL PHENOL HAVING FROM ABOUT 4 TO ABOUT 12 CARBON ATOMS IN THEIR CARBON CHAIN AND (4) FROM ABOUT 3% TO ABOUT 17% BY WEIGHT OF A FATTY MATERIAL SELECTED FROM THE GROUP CONSISTING OF A FARRY ACID HAVING A CARBON CHAIN LENGTH OF FROM ABOUT 8 TO ABOUT 22 CARON ATOMS, MIXTURES OF SAID FATTY ACIDS, AND MIXTURES OF SAID FATTY ACIDS WITH ESTERS PREPARED BY REACTING A FATTY ACID HAVING A CARBON CHAIN LENGTH OF FROM ABOUT 8 TO ABOUT 22 CARBON ATOMS AND MIXTURES THEREOF WITH MONOHYYDRIC ALIPHATIC ALCOHOLS HAVING A CARBON CHAIN OF FROM 1 TO ABOUT 5 CARBON ATOMS. 